Hydrochloric Acid → 3-Bromo-5-fluoroaniline

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(3-bromo-5-fluorophenyl)acetamide (Intermediate 181, 8.7 g, 37.4 mmol) in ethanol (30 mL) was added concentrated hydrochloric acid (80 mL). The reaction was heated to 100° C. for 1 hr. It was cooled to room temperature and neutralized with 5N sodium hydroxide. The crude product was extracted with ethyl acetate (2×100 mL), the combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated to dryness. Chromatography on silica gel with a gradient of 5-10% ethyl acetate in hexanes gave 5.3 g (75%) of the product as a yellow oil.

Provenance & Evidence